Alcohols such as allyl alcohols and styrallyl alcohols are useful as intermediates of drugs, agricultural chemicals, and the like. With respect to allyl alcohols, they can be converted into various compounds upon chemical conversion at a double bond site. Furthermore, it is thought that utilities are further widened by converting an alcohol into an optically active substance.
As a method for synthesizing such an optically active alcohol, there are chiefly reported two synthetic methods. One of them is a kinetic resolution method using Sharpless epoxidation, and the other is an asymmetric addition reaction of an alkenylzinc to a carbonyl compound. However, although these two methods are excellent, in the kinetic resolution method, the formation of by-products of a compound of an undesired stereospecific configuration is unavoidable; and in the asymmetric addition reaction of an alkenylzinc, there are encountered problems in application to mass synthesis and safety because this reagent itself is unstable in the presence of air or water. Thus, development of new synthetic methods has been demanded.
In recent years, a reaction using copper as a metal element for catalysts has been keenly studied. For example, there is reported an asymmetric addition reaction of an allyl group to a carbonyl group using a copper catalyst. J. Am. Chem. Soc., 2004, 126, 8910 describes allyboration of a ketone by using copper (II) fluoride/i-Pr-DuPHOS as a catalyst and adding a lanthanoid compound as an additive. Furthermore, JP-A-2003-311156 describes allylation of acetophenone with allyltrimethoxysilane by using copper (I) chloride/tol-BINAP/TBAT as a catalyst.
Furthermore, Tetrahedron Lett., 1979, 13, 1141 describes an addition reaction of an alkenyl group to a carbonyl compound with an alkenylfluorosilane by using a stoichiometric amount of a copper(I) salt, which is, however, not a catalytic reaction.